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  One-Point Binding Ligands for Asymmetric Gold Catalysis: Phosphoramidites with a TADDOL-Related but Acyclic Backbone

Teller, H., Corbet, M., Mantilli, L., Gopakumar, G., Goddard, R., Thiel, W., et al. (2012). One-Point Binding Ligands for Asymmetric Gold Catalysis: Phosphoramidites with a TADDOL-Related but Acyclic Backbone. Journal of the American Chemical Society, 134(37), 15331-15342. doi:10.1021/ja303641p.

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Teller, Henrik1, Autor           
Corbet, Matthieu1, Autor           
Mantilli, Luca1, Autor           
Gopakumar, Gopinadhanpillai2, Autor           
Goddard, Richard3, Autor           
Thiel, Walter2, Autor           
Fürstner, Alois1, Autor           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 Zusammenfassung: Readily available phosphoramidites incorporating TADDOL-related diols with an acyclic backbone turned out to be excellent ligands for asymmetric gold catalysis, allowing a number of mechanistically different transformations to be performed with good to outstanding enantioselectivities. This includes [2 + 2] and [4 + 2] cycloadditions of ene-allenes, cycloisomerizations of enynes, hydroarylation reactions with formation of indolines, as well as intramolecular hydroaminations and hydroalkoxylations of allenes. Their preparative relevance is underscored by an application to an efficient synthesis of the antidepressive drug candidate (−)-GSK 1360707. The distinctive design element of the new ligands is their acyclic dimethyl ether backbone in lieu of the (isopropylidene) acetal moiety characteristic for traditional TADDOL’s. Crystallographic data in combination with computational studies allow the efficiency of the gold complexes endowed with such one-point binding ligands to be rationalized.

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Sprache(n): eng - English
 Datum: 2012-04-162012-08-272012-09-19
 Publikationsstatus: Erschienen
 Seiten: 12
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1021/ja303641p
 Art des Abschluß: -

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Titel: Journal of the American Chemical Society
  Andere : J. Am. Chem. Soc.
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: American Chemical Society
Seiten: 12 Band / Heft: 134 (37) Artikelnummer: - Start- / Endseite: 15331 - 15342 Identifikator: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870
DOI: 10.1021/ja303641p